Benzylamine → HCID 276585, compound

HRID 488375Notes

Reaction equation

HRID 488375 reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[CH2:16][CH2:17]OS(C)(=O)=O)(=O)=O.[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[CH2:23]([N:30]1[CH2:17][CH2:16][C:8]2[C:7](=[CH:12][C:11]([N+:13]([O-:15])=[O:14])=[CH:10][CH:9]=2)[CH2:6]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 22269642HCID 22269642, compound

Product 1

HCID 276585HCID 276585, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [2-[2-[(methylsulfonyl)oxy]ethyl]-5-nitrophenyl]methyl methanesulfonate (Step 1, 1.75 g, 4.95 mmol) in CH2Cl2 (25 mL) under N2 is treated with benzylamine (2.70 mL, 24.75 mmol), and the resulting mixture is stirred at ambient temperature for 24 hrs and then washed with water (20 mL) and brine (10 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product is then chromatographed on a Flash 40M silica gel (90 g, 32-63 μm) cartridge, eluting with EtOAc/heptane (10/90), and those fractions with an Rf=0.32 by TLC (EtOAc/hexane, 25/75) are pooled and concentrated to give 1.33 g (100%) of the title compound as an orange solid, mp 85-86° C.

Workup

  1. washwashed with water (20 mL) and brine (10 mL)
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product is then chromatographed on a Flash 40M silica gel (90 g, 32-63 μm) cartridge
  5. washeluting with EtOAc/heptane (10/90)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ed4974c273434da0b773f0058c91bb66
Source dataset
uspto-grants-2005_12
Patent number
US06972286B2

Reaction notes

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